Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Chlorobenzoxazole | HCID 11986 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,1-Dichloroethane | HCID 6365 | — |
| Product | HCID 68278456 | HCID 68278456 | — |
Reaction Steps
A mixture of bis(triphenylphosphine)palladium(II) chloride (0.229 g, 0.326 mmol), triethylamine (1.815 mL, 13.02 mmol), copper(I) iodide (0.124 g, 0.651 mmol), trimethylsilylacetylene (29A, 1.645 mL, 11.72 mmol) and compound 28A (1.0 g, 6.51 mmol) in dichloroethane (10 mL) under an inert atmosphere was heated at 80° C. overnight. After the reaction was complete, the mixture was cooled, diluted with dichloromethane (10 mL), washed with aq. NaHCO3, dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with 0-5% EtOAc/hexanes to give a mixture of Compound 29B (575 mg) and Compound 29C (200 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08927559B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-165049813bab4a1cacc2175dfd1d5940 |
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| Source note | uspto-grants-2015_01 |
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